A highly active catalyst for Pd-catalyzed amination reactions: cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides.

作者: Brett P. Fors , Donald A. Watson , Mark R. Biscoe , Stephen L. Buchwald

DOI: 10.1021/JA8055358

关键词: Buchwald–Hartwig aminationChemistryPalladiumArylCoupling reactionAminationReactivity (chemistry)CatalysisOrganic chemistryOxidative addition

摘要: A catalyst system based on a new biarylmonophosphine ligand (BrettPhos) that shows excellent reactivity for C−N cross-coupling reactions is reported. This catalyst system enables the …

参考文章(23)
Rachel H. Munday, Joseph R. Martinelli, Stephen L. Buchwald, Palladium-catalyzed carbonylation of aryl tosylates and mesylates. Journal of the American Chemical Society. ,vol. 130, pp. 2754- 2755 ,(2008) , 10.1021/JA711449E
Christian Amatore, Emmanuelle Carre, Anny Jutand, Mohamed Amine M'Barki, Rates and Mechanism of the Formation of Zerovalent Palladium Complexes from Mixtures of Pd(OAc)2 and Tertiary Phosphines and Their Reactivity in Oxidative Additions Organometallics. ,vol. 14, pp. 1818- 1826 ,(1995) , 10.1021/OM00004A039
John P. Wolfe, Stephen L. Buchwald, Scope and Limitations of the Pd/BINAP-Catalyzed Amination of Aryl Bromides Journal of Organic Chemistry. ,vol. 65, pp. 1144- 1157 ,(2000) , 10.1021/JO9916986
Franck Rataboul, Alexander Zapf, Ralf Jackstell, Surendra Harkal, Thomas Riermeier, Axel Monsees, Uwe Dingerdissen, Matthias Beller, New ligands for a general palladium-catalyzed amination of aryl and heteroaryl chlorides. Chemistry: A European Journal. ,vol. 10, pp. 2983- 2990 ,(2004) , 10.1002/CHEM.200306026
Takashi Ikawa, Timothy E. Barder, Mark R. Biscoe, Stephen L. Buchwald, Pd-Catalyzed Amidations of Aryl Chlorides Using Monodentate Biaryl Phosphine Ligands: A Kinetic, Computational, and Synthetic Investigation Journal of the American Chemical Society. ,vol. 129, pp. 13001- 13007 ,(2007) , 10.1021/JA0717414
Mark R. Biscoe, Brett P. Fors, Stephen L. Buchwald, A New Class of Easily Activated Palladium Precatalysts for Facile C−N Cross-Coupling Reactions and the Low Temperature Oxidative Addition of Aryl Chlorides Journal of the American Chemical Society. ,vol. 130, pp. 6686- 6687 ,(2008) , 10.1021/JA801137K
Fumiyuki Ozawa, Akihiko Kubo, Tamio Hayashi, Generation of Tertiary Phosphine-Coordinated Pd(0) Species from Pd(OAc)2in the Catalytic Heck Reaction Chemistry Letters. ,vol. 21, pp. 2177- 2180 ,(1992) , 10.1246/CL.1992.2177
Brett P. Fors, Philipp Krattiger, Eric Strieter, Stephen L. Buchwald, Water-mediated catalyst preactivation: an efficient protocol for C-N cross-coupling reactions. Organic Letters. ,vol. 10, pp. 3505- 3508 ,(2008) , 10.1021/OL801285G